Water → HCID 90449730, compound

HRID 1411306Notes

Reaction equation

HRID 1411306 reaction equation
[C:1]([S:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:17]3([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)[CH2:16][N:15]([C:29]([O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])=[O:30])[C:12]2=[CH:13][CH:14]=1)(=O)C.[OH-].[Na+].IC.O>CO.O1CCCC1>[CH3:1][S:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:17]3([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)[CH2:16][N:15]([C:29]([O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])=[O:30])[C:12]2=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 90449543HCID 90449543, compound

Product 1

HCID 90449730HCID 90449730, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-(4-(acetylthio)butyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (89.2 mg, 0.163 mmol) was dissolved in methanol (1.5 mL) and tetrahydrofuran (1.5 mL). Thereafter, a 4 N aqueous solution of sodium hydroxide (0.4 mL, 1.6 mmol) and iodomethane (51 μL, 0.815 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 1 hour. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo, to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(4-(methylthio)butyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (85 mg, quant.) in the form of a brown oily product.

Workup

  1. extractionthe mixed solution was then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-438e115d01024ac882b9badabf073fd8
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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